


Paying Off Debts

by ScotchAfterDark



Category: Supernatural
Genre: Abusive John Winchester, Anal Fingering, Anal Sex, Bondage, Bottom Dean Winchester, Dead Dove: Do Not Eat, Gang Rape, Homophobic John Winchester, Homophobic Language, John Winchester Being an Asshole, M/M, Rape/Non-con Elements, Repaying Debt, Rough Oral Sex, Rough Sex
Language: English
Status: Completed
Published: 2020-11-18
Updated: 2020-11-18
Packaged: 2021-03-09 19:08:54
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 2,213
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27611159
Author URL: https://archiveofourown.org/users/ScotchAfterDark/pseuds/ScotchAfterDark
Summary: John Winchester owes a lot of money. When he catches Dean screwing around with Lee, he knows how to make that money back and then some.
Relationships: Dean Winchester/Other(s)
Comments: 1
Kudos: 78





	Paying Off Debts

**Author's Note:**

> While there is no incest in this fic, one of the characters does tell John he should try Dean for himself.

“Dad, please. No.” Dean pulled against the restraints tying him to the bed. He was face down, his knees tucked under him, ass in the air. “I said I’d stop seeing him.”

“You think I’m stupid, boy?” John sat in the corner of the room, out of Dean’s line of sight. “I know the moment you go out on your own, you’re gonna go find the little faggot and let him claim you.” Dean could hear John spit the words out of his mouth, and he flinched at the sound. “This? What you’re doing? This is for his freedom and to help pay off a little debt I owe.”

A knock on the door made Dean jump. He turned his head to see his father walk over to open it. In walked several men, some Dean knew, some he didn’t. And it was clear they were all here for the same thing.

Him.

“Alright, boys. There’s a box of condoms on the table, as well as a bottle of lube. If you want to bareback him, I need papers provin’ you’re clean, and it’s an extra hundred.”

Dean pulled harder on the restraints, desperate to escape, desperate to flee. “Dad, no!”

“Sorry, guys. Forgot to do something.” John walked back over to the bed and grabbed a bandana off the nightstand. He yanked Dean’s hair pulling Dean’s head up sharply and shoved the fabric deep into his mouth. John leaned in close to Dean’s ear. “No need to tie. Some of these guys want your mouth, Dean. You bite, they’re allowed to make you lose a few teeth.”

Dean whimpered into the makeshift gag as he tried to fight back his tears. He had gotten too lax, too carefree with Lee. He knew his father wouldn’t have approved of their relationship, but he never expected his father to go this far.

After some small discussion - it sounded almost like the men were bidding on who’d get his ass first - Dean watched as his father took a wad of cash from one of the hunters he didn’t know. The man stopped at the nightstand and dug a condom out of the box. Dean watched helplessly as the man undid his pants and pushed them down enough to pop out his cock. It wasn’t anything to write home about, and Dean let out a prayer for small mercies.

The hunter stroked himself hard, his cock leaking precum, before rolling the condom on. He squeezed out a generous amount of lube onto his hand and continued stroking himself as he climbed on the bed behind Dean.

“Looks like Daddy raised a pretty little whore. Glad he was finally smart enough to see how much money he could make off of you.” With little fanfare, but a lot of force, the hunter slammed into Dean, causing Dean to scream into the gag. “That’s it. Scream like the little bitch you are. Cause if you think this is a lot? Wait until Gordon over there gets his monster in you.” The man dug his fingers painfully into Dean’s hips, nearly lifting him off the bed as he fucked into him. There was no care. No concern. Just the carnal need to get off.

What seemed like a lifetime - but probably three minutes at most - later, the seized and grunted as he came. “Hot damn, John. I’m sure you ain’t proud, but your boy’s a champ.”

“I don’t need to know, Martin.” Dean looked for his father, but couldn’t find him. “You’ve had your turn. Let the next person up.”

The weight behind Dean shifted on the bed, and the hunter - Martin - grabbed a marker off the nightstand and dragged it down Dean’s ass cheek. “It’s always nice to be number one.” He whispered in Dean’s ear as he stepped away. Martin was quickly replaced by another - Dean didn’t get a chance to see who it was, as the hunter had obscured his view - and Dean felt another cock slam into him.

“Martin, how tiny is that prick of yours? You did nothing to warm up our little bitch.” The new hunter slid out and pushed in slowly, and Dean was thankful for the small reprieve. Until the new cock pulled out and slammed back in. Dean cried out, his sounds muffled by the drool soaked bandana stuck in his mouth. Each thrust from the hunter caused sparks to fly, and Dean hated it. 

“The bitch likes it. Fuck him harder!” Dean closed his eyes shut tighter as one of the men in the room yelled out. 

“Oh yeah.” The hunter who was fucking him reached forward and grabbed his hair, pulling it harshly as he forced Dean to look ahead and arch his back. “You’re enjoying this, ain’t ya? Well, it’s not for you to like. You’re just my little fuck toy today.” He shoved Dean’s head back down and increased his already brutal pace. After a few moments, the man growled as he came. He slipped out of Dean, and just like Martin before him, he grabbed the marker off the nightstand and marked a notch on Dean’s ass.

“Your boy keeps this up, John; some of us might want seconds.”

A snort sounded out from behind Dean. “You pay for it? You can fuck him as much as you want.”

“Looks like you might pay off your debt then tonight.” Dean looked up at the next hunter who was coming to fuck him. He recognized him, Travis, another one of his old man’s hunting buddies. “Is he gonna bite if I fuck that pretty mouth of his?”

“I already warned him that if he tries, you can bash his teeth in.” Dean tried to pull away as John answered, but Travis quickly grabbed the back of his head as he unzipped. “If you’re not putting on a condom, it’s an extra hundred dollars.”

“I’m good for it.” Travis climbed up onto the bed and pulled the bandana out of Dean’s mouth. “One bite and I destroy your moneymaker, bitch.” He quickly forced his cock down Dean’s throat, causing Dean to gag and gasp for air. “Just let it happen, bitch. The sooner you relax, the sooner you’ll get your prize for makin’ me feel good.”

Dean continued gagging, each thrust from Travis fucking his face causing his stomach to coil in disgust. He couldn’t breathe, and he thrashed against his restraints. Dean needed to pull away. He needed air.

“Ah, fuck!” Travis forced his cock down Dean’s throat one last time, coming hard enough that what Dean couldn’t swallow came up through his nose instead. Dean gasped for breath, sputtering and sneezing out the come he couldn’t take. 

“Dad, please!” Dean cried out. “I promise. Please! Make them stop.” 

John came into view and picked up the bandana Travis had thrown haphazardly on the floor. “I haven’t made my money back, and they’re not done yet. You got at least two men left, assuming no one wants seconds.” He shoved the fabric square back into Dean’s mouth. “We make sacrifices, right?” He stepped back and out of view. “He’s yours now, Kubrick.”

“‘Bout damn time.” A raspy voice sent chills down Dean’s spine.

When Dean realized he didn’t see the hunter come up to grab a condom, he started fighting against his bindings. He begged for Kubrick to put one on, but his words were lost to the muffle of the bandana.

“What was that, little whore? Fuck you raw?” The sound of a bottle clicking open caused Dean to fight more. “I can’t wait to hear you squeal like the pig you are.”

Dean cried out as Kubrick slid in, the skin-on-skin more offensive than the actual fucking. Dean had never got to this point with Lee; that opportunity was taken from him. He whimpered into his gag, giving up and losing his fight as the hunter railed into him, fucking him harder and rougher than Martin and the other unknown hunter had.

A harsh slap to his ass cheek caused Dean to grunt out in pain, and Kubrick laughed sadistically. “I want to hear you. I will not stop until you are screaming into that gag, you little bitch. You want this over with? You let me hear you.” Another slap across his ass and his hair being pulled back again caused Dean to wail. “That’s it. Daddy’s little boy gonna take all of my come.”

Dean winced in pain as Kubrick’s other hand dug into his hip, and he knew there’d be – at the very least – bruises there when all was said and done.

“Ugh, such a good little slut. Take it, you worthless piece of garbage. Only thing you're good for is taking the loads of Daddy’s friends.” Kubrick’s movements became frantic, and after a moment, he stopped, his hot come filling Dean. “That’s the best fucking load I’ve ever shot. Figures a hot young piece of ass like you could draw it out of me.” The hunter slid out of Dean, giving his ass another slap before adding another mark onto his ass. “I know he’s your boy, John, but you should really give him a ride.”

“No. Get the fuck out, Kubrick.” At least John sounded disgusted by Kubrick’s suggestion. But it wasn’t long before he talked to the last hunter in the room. “Gordon?”

Gordon walked over and stood next to the bed so Dean could see him. “When I’m done with you, boy, you’re going to think the other guys were being kind.” The final hunter slowly undid his belt before opening his pants. Dean blanched at the outline of the cock tenting Gordon’s boxers. “Your old man didn’t buy condoms big enough for me, so you’re going to feel every last inch of this.” Gordon leaned into Dean. “And you’re never going to have enough cock filling you when this is all over. You’ll be calling me, begging for more.”

Dean buried his face in the mattress, whimpering. Gordon’s cock was nothing to scoff at and, because Dean didn’t have a choice, it would be buried inside of him.

The bed shifted as Gordon climbed behind Dean. Unlike the previous hunters, Gordon took a moment to prep him, fingering his ass, stretching it out. “If you’re too tight, it’ll hurt me,” Gordon commented. Once he was deemed ready, Gordon lined himself up and started to press his cock inside Dean’s tight ass. Dean pulled against the straps holding him down, crying into his gag as Gordon entered him. It hurt, fuck did it hurt, but the size meant that everything was getting hit.

“Feels good, doesn’t it, whore?” Gordon asked once he was fully sheathed. “I told you, once you had me, you’re never going to want to fuck another person. You’re going to be Daddy’s good little slut and spread out every time he needs money.” He pulled out slowly, his cock dragging across Dean’s prostate, causing Dean to cry out in pleasure for the first time since his assault began. “That’s right. You’re going to beg me to come.”

Dean shook his head. He wasn’t going to beg. He wasn’t going to ask for release. Dean wouldn’t give Gordon the benefit of the doubt. Until Gordon started to push back in. It was harder and faster than his previous entrance, and Dean saw stars behind his eyelids. He moaned in pleasure - despite not wanting to - and gripped the bed, bracing as each thrust fucked him deeper into the mattress.

“Who’s a good piggy, getting stuffed and fucked? You’re gonna come before I am. I know it. You’ve slept with your boy toy. You’ve been filled by four other men. Now you’re about to used and abused, you little bitch.” Gordon bent over Dean and pressed him into the bed as he started to rail into him. “I won’t even have to touch you. You’re going to come, and then I’m going to keep fucking you while you beg me to stop.”

Dean keened into his gag. Gordon was absolutely right. The deeper thrusts and faster rhythm was pushing him closer and closer to coming. After an incredibly sharp tug to his hair, Dean screamed as his orgasm was punched out of him.

“Fucking told you.” Gordon picked up the pace. “John, anytime we’re in the same town, just call me. I’ll be more than happy to keep your little slut broken in for you.”

“Might take you up on that.”

Dean’s fingers dug into the mattress as Gordon continued to fuck him. As the hunter promised, Dean quickly became oversensitive and was crying with each continued thrust. After several pleas that went unheard, Gordon stiffened up behind Dean, and the rush of hot come filled Dean’s ass again. Gordon slid out with a pop, and Dean could feel the wet, sticky mess dripping down his inner thigh.

With a slap to his ass and another drag of the marker across his skin, Dean passed out.

…

Sometime later - it could have been minutes or hours, he wasn’t sure - Dean woke up, still tied down to the bed. The gag had been removed, and Dean was desperate for water. As he tried to look around, his father’s voice startled him from behind.

“Ready for the next group?”


End file.
